WO2021133137A1 - Procédé de préparation de 1,4-cyclohexanediméthanol - Google Patents

Procédé de préparation de 1,4-cyclohexanediméthanol Download PDF

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Publication number
WO2021133137A1
WO2021133137A1 PCT/KR2020/019186 KR2020019186W WO2021133137A1 WO 2021133137 A1 WO2021133137 A1 WO 2021133137A1 KR 2020019186 W KR2020019186 W KR 2020019186W WO 2021133137 A1 WO2021133137 A1 WO 2021133137A1
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Prior art keywords
cyclohexanedimethanol
reaction
weight
producing
dicarboxylic acid
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PCT/KR2020/019186
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English (en)
Korean (ko)
Inventor
장남진
이선욱
김은정
이종권
Original Assignee
한화솔루션 주식회사
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Priority claimed from KR1020200183549A external-priority patent/KR20210084311A/ko
Application filed by 한화솔루션 주식회사 filed Critical 한화솔루션 주식회사
Priority to JP2022539243A priority Critical patent/JP2023508201A/ja
Priority to EP20905622.5A priority patent/EP4082999A4/fr
Priority to US17/789,456 priority patent/US20230053503A1/en
Priority to CN202080093297.4A priority patent/CN114945546A/zh
Publication of WO2021133137A1 publication Critical patent/WO2021133137A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C31/00—Saturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
    • C07C31/27—Polyhydroxylic alcohols containing saturated rings
    • C07C31/272—Monocyclic
    • C07C31/276—Monocyclic with a six-membered ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
    • C07C29/132—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
    • C07C29/136—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH
    • C07C29/147—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of carboxylic acids or derivatives thereof
    • C07C29/149—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of carboxylic acids or derivatives thereof with hydrogen or hydrogen-containing gases
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J21/00—Catalysts comprising the elements, oxides, or hydroxides of magnesium, boron, aluminium, carbon, silicon, titanium, zirconium, or hafnium
    • B01J21/18—Carbon
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
    • B01J23/14—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of germanium, tin or lead
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
    • B01J23/38—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals
    • B01J23/40—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals of the platinum group metals
    • B01J23/46—Ruthenium, rhodium, osmium or iridium
    • B01J23/462—Ruthenium
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
    • B01J23/38—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals
    • B01J23/54—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36
    • B01J23/56—Platinum group metals
    • B01J23/62—Platinum group metals with gallium, indium, thallium, germanium, tin or lead
    • B01J23/622—Platinum group metals with gallium, indium, thallium, germanium, tin or lead with germanium, tin or lead
    • B01J23/626—Platinum group metals with gallium, indium, thallium, germanium, tin or lead with germanium, tin or lead with tin
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B2200/00—Indexing scheme relating to specific properties of organic compounds
    • C07B2200/09—Geometrical isomers

Definitions

  • the present invention relates to a method for producing 1,4-cyclohexanedimethanol (1,4-cyclohexanedimethanol, CHDM). More specifically, it relates to a method for producing 1,4-cyclohexanedimethanol having a high trans isomer ratio even without including an isomerization step.
  • 1,4-cyclohexanedimethanol (1,4-cyclohexanedimethanol, CHDM) is widely used as a raw material for pharmaceuticals, synthetic resins, synthetic fibers, or dyes, and is particularly used as a raw material for polyethylene terephthalate, an eco-friendly polyester.
  • 1,4-cyclohexanedimethanol exists as stereoisomers in cis and trans forms.
  • trans 1,4-cyclohexanedimethanol (trans CHDM) is used rather than cis. A high ratio is required.
  • an isomerization reaction of 1,4-cyclohexane dicarboxylic acid (CHDA) is performed to increase the trans content, followed by a hydrogenation reaction with CHDM, hydrogenation of CHDA
  • CHDM 1,4-cyclohexane dicarboxylic acid
  • the conventional method of additionally performing the isomerization reaction has disadvantages that are not commercially desirable because the process is complicated, inefficient, and requires additional production costs.
  • Patent Document 0001 International Patent Publication No. 2019-046412
  • Patent Document 0002 Korean Patent Registration No. 10-1639487
  • the present invention is to solve the above problems, by adjusting the concentration of 1,4-cyclohexane dicarboxylic acid (CHDA) as a reactant, even without including an isomerization reaction step
  • An object of the present invention is to provide a method for preparing 1,4-cyclohexanedimethanol having a high ratio of trans isomers.
  • the 1,4-cyclohexane dicarboxylic acid is included in an amount of 5 to 30% by weight based on the total amount of 1,4-cyclohexane dicarboxylic acid and water,
  • a method for preparing 1,4-cyclohexanedimethanol is provided.
  • Another embodiment of the present invention provides a composition comprising 1,4-cyclohexanedimethanol prepared by the above preparation method.
  • 1,4-cyclohexane 1,4-cyclohexanedimethanol having a high ratio of trans isomers can be prepared by controlling the concentration of hexane dicarboxylic acid.
  • the process can be simplified and economical by not performing an additional isomerization step, and the high trans isomer content of the prepared CHDM can be expected to improve physical properties when used as a polymer raw material.
  • 1,4-cyclohexane dicarboxylic acid containing a cis isomer and a trans isomer, a hydrogenation catalyst, and water in a reactor equipped with a stirrer supplying a reaction solution comprising; supplying hydrogen gas to the reactor into which the reaction solution is introduced; and preparing 1,4-cyclohexanedimethanol (CHDM) by performing a hydrogenation reaction by stirring the stirrer of the reactor, wherein the 1,4-cyclohexanedicarboxylic acid is 1 , It provides a method for producing 1,4-cyclohexanedimethanol, which is contained in an amount of 5 to 30% by weight based on the total amount of ,4-cyclohexane dicarboxylic acid and water.
  • CHDA 1,4-cyclohexane dicarboxylic acid
  • 1,4-cyclohexanedimethanol is prepared by performing a hydrogenation reaction on 1,4-cyclohexanedicarboxylic acid in the presence of a hydrogenation catalyst
  • 1,4-cyclohexanedimethanol obtained as the reaction product is Cis and trans isomers, that is, cis CHDM (cis CHDM) and trans CHDM (trans CHDM) are obtained in a mixed form.
  • 1,4-cyclohexanedimethanol having a high trans content
  • an isomerization reaction step of converting the cis isomer into the trans isomer was essentially accompanied.
  • 1,4-cyclohexane dicarboxylic acid is used as a raw material for the isomerization reaction to obtain 1,4-cyclohexane dicarboxylic acid with an increased trans content, and the trans content is used again as a hydrogenation reaction raw material.
  • This high 1,4-cyclohexanedimethanol is prepared, or 1,4-cyclohexanedicarboxylic acid, which is a raw material, is first hydrogenated, and then the obtained 1,4-cyclohexanedimethanol is isomerized to form a trans content.
  • This improved 1,4-cyclohexanedimethanol was prepared.
  • the process is complicated due to an additional isomerization process, which is inefficient and requires additional production costs, which is not commercially desirable.
  • the isomer converting the cis isomer into the trans isomer by adjusting the concentration of 1,4-cyclohexanedicarboxylic acid as a reaction raw material. It was possible to prepare 1,4-cyclohexanedimethanol containing a high content of trans isomer without including a chemical reaction step.
  • the concentration of 1,4-cyclohexanedicarboxylic acid is within a certain range
  • the product 1,4-cyclohexanedimethanol is formed without including an additional isomerization reaction step.
  • An unexpected effect of increasing the trans isomer content compared to the reactant was confirmed. This is because the isomerization rate varies according to the concentration of 1,4-cyclohexanedicarboxylic acid, and the time for the thermodynamically trans/cis isomer ratio to reach equilibrium becomes shorter as the isomerization rate increases at a certain concentration. see.
  • 1,4-cyclohexane dicarboxylic acid containing a cis isomer and a trans isomer in a reactor equipped with a stirrer (A reaction solution containing 1,4-cyclohexane dicarboxylic acid (CHDA), a hydrogenation catalyst, and water is supplied.
  • CHDA 1,4-cyclohexane dicarboxylic acid
  • the 1,4-cyclohexane dicarboxylic acid is included in an amount of 5 to 30% by weight based on the total amount of 1,4-cyclohexane dicarboxylic acid and water. More specifically, 5% by weight or more, or 7% by weight or more, or 10% by weight or more, and 30% by weight or less, or 25% by weight or less, or 23% by weight or less.
  • the contact between the reactant and the catalyst is reduced to slow the reaction rate, or in the generated CHDM
  • the ratio of the trans isomer is reduced, and when it exceeds 30 wt%, the solubility of 1,4-cyclohexanedicarboxylic acid is lowered to decrease productivity, and accordingly, the amount of crystals and catalysts of the reactants increases to feed the slurry. There may be difficulties in the process.
  • the ratio of the cis isomer and the trans isomer of 1,4-cyclohexane dicarboxylic acid as a starting material for the reaction, but in the 1,4-cyclohexane dicarboxylic acid, the ratio of the trans isomer is 60 wt% or more, or 62 wt% or more, or 65 wt% or more, or 67 wt% or more, or 70 wt% or more, and there is no upper limit on the proportion of trans isomers, but for example 80 wt% or less, or 78 wt% or less, or 75 wt% or less % or less.
  • the hydrogenation catalyst is one or more metals selected from the group consisting of palladium (Pd), rhodium (Rh), and ruthenium (Ru) as active ingredients, tin (Sn), iron ( Fe), rhenium (Re), and may include one or more metals selected from the group consisting of gallium (Ga), respectively.
  • ruthenium (Ru) and tin (Sn) may be included as active components of the hydrogenation catalyst. More preferably, the active components of the hydrogenation catalyst are made of only ruthenium (Ru) and tin (Sn), and may not include other active components.
  • the amount of the active component of the hydrogenation catalyst may be appropriately controlled according to the content of the reactant CHDA. Specifically, the higher the content of the hydrogenation catalyst compared to CHDA, the higher the reaction rate. Therefore, in the method for producing CHDM according to an embodiment of the present invention, the hydrogenation catalyst is added in an amount such that the weight ratio of the hydrogenation catalyst to CHDA is 0.01:1 or more. can be
  • the hydrogenation catalyst is more specifically the weight ratio of the active ingredient to CHDA of the hydrogenation catalyst 0.01: It may be added in an amount to satisfy 1 to 3:1.
  • the hydrogenation catalyst has a weight ratio of the hydrogenation catalyst to CHDA of 0.01:1 to 3:1, or 0.1:1 to 3:1, or 0.1:1 to It may be more preferable to add it in an amount such that it is 2:1.
  • the above weight ratio does not limit the scope of the present invention, and the ratio of the catalyst may be appropriately adjusted according to detailed reaction conditions and types of reactors.
  • Such a hydrogenation catalyst may be used by being supported on a carrier, and as the carrier, a carrier known in the art may be used without limitation. Specifically, a carrier such as carbon, zirconia (ZrO 2 ), titania (TiO 2 ), alumina (Al 2 O 3 ), or silica (SiO 2 ) may be used.
  • a carrier such as carbon, zirconia (ZrO 2 ), titania (TiO 2 ), alumina (Al 2 O 3 ), or silica (SiO 2 ) may be used.
  • ruthenium (Ru) and tin (Sn) when included as active components of the hydrogenation catalyst, ruthenium (Ru) and tin (Sn) are, with respect to 100 parts by weight of the entire carrier, Each may be included in an amount of 1 to 20 parts by weight, or 1 to 10 parts by weight, or 3 to 8 parts by weight.
  • At least one selected from the group consisting of activated carbon, carbon black, graphite, graphene, ordered mesoporous carbon (OMC) and carbon nanotubes may be used.
  • the activated carbon is SXULTRA, CGSP, PK1-3, SX 1G, DRACO S51HF, CA-1, A-51, GAS 1240 PLUS , KBG, CASP and SX PLUS, and the like, and the carbon black may be BLACK PEARLS®, ELFTEX®, VULCAN®, MOGUL®, MONARCH®, EMPEROR®, REGAL®, etc., but is not limited thereto.
  • the volume ratio of mesopores having a pore size of 2 to 50 nm among all pores of the carbon may be 50% or more.
  • the carbon in the carbon carrier has a volume ratio of mesopores in the total pores of 70% or more, and more preferably, the carbon in the carbon carrier has a volume ratio of mesopores in the total pores of 75% or more. .
  • the volume ratio of the mesopores is less than 50%, there may be a problem of the microscopic mass transfer rate in the carbon carrier of the reactants and products, and when the average size of the pores is more than 50 nm, the physical strength of the carrier is weak. may exist, so the above range is suitable.
  • the carbon includes ordered mesoporous carbon (OMC) having a specific surface area (BET) in the range of 100 to 1,500 m 2 /g.
  • the carbon may include ordered mesoporous carbon (OMC) having a specific surface area (BET) in the range of 200 to 1,000 m 2 /g.
  • OMC ordered mesoporous carbon
  • BET specific surface area
  • the specific surface area of the carbon is less than 100 m 2 /g, there may be a problem in that high dispersion of active metals (Ru, Sn) is difficult, and the specific surface area of the carbon exceeds 1,500 m 2 /g Since there may be a problem that the ratio of mesopores decreases, the above range is suitable.
  • the carbon carrier of the catalyst according to the present invention contains micropores in an appropriate ratio in addition to medium-sized mesoporosity, and preferably, the volume ratio of micropores in the total pores is 0 to 25% may be included. At this time, when the volume ratio of the micropores exceeds 25%, there may be a problem of microscopic mass transfer rates in the carbon carrier of the reactants and products, so the above range is suitable.
  • the amount of the active ingredient of the hydrogenation catalyst is preferably 20 parts by weight or less, 15 parts by weight or less, or 10 parts by weight or less, and 1 part by weight or more, or 3 parts by weight based on 100 parts by weight of the carrier. It may be more than 1 part by weight. If the amount of the hydrogenation catalyst is too large compared to 100 parts by weight of the carrier, the reaction proceeds rapidly on the surface of the catalyst, and in this process, side reactions also increase, which may cause a problem in which the amount of by-products increases rapidly, and if too small, the amount of catalyst is insufficient. The above range is preferable because the yield of the hydrogenation reaction may decrease.
  • the method for producing 1,4-cyclohexanedimethanol according to an embodiment of the present invention may be performed using a reactor including a stirrer, a raw material input unit, a metal sintering filter, and a product discharge unit.
  • the agitator is a gas-induced type agitator, and may include a gas inlet, a gas passageway, an impeller, and an injection port.
  • the stirrer is provided in the upper and lower directions of the reactor, and may include a gas inlet at the upper portion for sucking gas, that is, hydrogen gas by centrifugal force.
  • the hydrogen gas sucked into the gas inlet moves to the lower part of the reactor through the gas passage passage.
  • the hydrogen gas moved to the lower part of the reactor may be injected and supplied to the reaction solution through a plurality of injection holes provided in the stirrer to perform a hydrogenation reaction.
  • the injection port may be located at the lower part, the side surface, or both the lower part and the side surface of the stirrer.
  • the hydrogen gas sucked through the gas inlet is injected into the reaction solution through a plurality of injection holes provided in the stirrer, and the hydrogenation reaction rate is increased as the hydrogenation reaction is performed while mixing.
  • the stirrer since the stirrer includes an impeller and the impeller stirs the reaction solution, a gas holdup rate and a surface area per unit volume may increase. Accordingly, the hydrogenation reaction rate in the reactor can be increased.
  • the impeller may be disposed in a plurality of stages on the rotating shaft of the agitator.
  • only an impeller having an injection hole at the bottom of the stirrer is provided, and an additional impeller may not be provided.
  • the rotating shaft may be driven by a driving motor provided outside.
  • the lower portion of the reactor may be connected to a reaction raw material input unit, and a reaction raw material, that is, terephthalic acid, a solvent, and hydrogen gas may be introduced.
  • the reactor may include a metal sintered filter for filtering the catalyst from the product and a product discharge unit
  • the metal sintered filter may be installed connected to the product discharge unit.
  • the metal sintered filter may be connected to the product discharge unit and provided outside the reactor. The metal sintered filter can effectively filter the catalyst component remaining in the product.
  • the hydrogenation reaction may be carried out in a liquid phase or a gas phase.
  • the 1,4-cyclohexanedicarboxylic acid may be in a liquid phase dissolved in a solvent such as water, and hydrogen may be hydrogenated in a gaseous state.
  • 1,4-cyclohexanedimethanol is prepared by performing a hydrogenation reaction by stirring the stirrer of the reactor.
  • the hydrogenation reaction conditions are not particularly limited, but for example, the reaction temperature may be 230°C or higher, 300°C or lower, or 280°C or lower, or 270°C or lower. If the reaction temperature is less than 230 °C, the contact between the reactant and the catalyst is reduced, the reaction rate is lowered out of the operable temperature range of the catalyst, or the content of the trans isomer in the produced CHDM is reduced, and when it exceeds 300 °C, the by-product is may increase rapidly. The above range is preferred as it may also affect the catalyst life.
  • reaction pressure may be 50 bar or more, or 80 bar or more, and 220 bar or less, or 200 bar or less, or 180 bar or less. If the reaction pressure is less than 50 bar, the reaction does not occur well, an excessive amount of catalyst is consumed, the residence time is too long, so there may be various problems such as an increase in by-products, and if it exceeds 220 bar, the process operation
  • the above range is preferable because there may be a problem in that energy such as excessive power is required, and the manufacturing cost of equipment such as a reactor is greatly increased.
  • reaction pressure is a pressure set by the supplied hydrogen gas, it may be adjusted according to the supply amount of the hydrogen gas.
  • a stirring process is performed during the hydrogenation reaction, and reaction efficiency during the hydrogenation reaction can be increased by controlling the speed during the stirring process.
  • the stirring process may be performed so that the surface area per unit volume of the hydrogen gas bubble is 15 m 2 /m 3 or more. more specifically 50 m 2 /m 3 or more, or 100 m 2 /m 3 or more, or 150 m 2 /m 3 or more, or 200 m 2 /m 3 , Or 300 m 2 /m 3 or more may be performed.
  • the surface area per unit volume satisfies a certain level, for example, 15 m 2 /m 3 or more, the reaction rate is slower than the rate at which hydrogen gas is dissolved in the range beyond that, so that the reaction rate is not significantly affected. Therefore, the surface area per unit volume only needs to satisfy 15 m 2 /m 3 or more, and the upper limit is not significantly limited because there is no significant influence, but it is preferably 500 m 2 /m 3 or less in consideration of the energy efficiency of the reactor.
  • the stirring process may be performed using the stirring device of the reactor described above.
  • the reaction product obtained after the reaction includes CHDM including cis and trans isomers, water as a solvent, catalyst, and the like, and can be used as a reactant for various reactions. If necessary, by-products, solvents, catalysts, etc. included in the reaction product may be used after removal by a purification process.
  • the content of the total CHDM including the cis isomer and the trans isomer in the total weight of the step reaction product is 5 to 30% by weight. More specifically, 5% by weight or more, or 7% by weight or more, or 10% by weight or more, and 30% by weight or less, or 25% by weight or less, or 23% by weight or less.
  • CHDA in a mixed solution containing CHDA, a hydrogenation catalyst and water is 5 to 30% by weight, 7 to 30% by weight, based on the total amount of 1,4-cyclohexanedicarboxylic acid and water
  • the proportion of the trans isomer in the total CHDM prepared is 63% by weight or more, or 65% by weight % or more, or 67 wt% or more, or 69 wt% or more, or 70 wt% or more, and there is no upper limit on the proportion of trans isomers, but for example 99 wt% or less, or 95 wt% or less, or 90 wt% or less , or 85% by weight or less.
  • 1,4-cyclohexanedimethanol finally obtained by the production method of the present invention has an excellent trans isomer content of 63% by weight or more, so it is useful as a raw material for manufacturing a higher quality product without an additional isomerization process can be used
  • Another embodiment of the present invention provides a composition comprising 1,4-cyclohexanedimethanol prepared by the method for preparing 1,4-cyclohexanedimethanol.
  • 1,4-cyclohexanedimethanol as a raw material or reactant for another process without an isomerization process
  • the content of the trans isomer in 1,4-cyclohexanedimethanol is required to be 63% by weight or more.
  • the content of the trans isomer in 1,4-cyclohexanedimethanol is 63 wt% or more, 65 wt% or more, 67 wt% or more, 69 wt% or more It may have a very high trans isomer content of greater than or equal to 70% by weight or greater.
  • the proportion of the trans isomer may be 99 wt% or less, 95 wt% or less, 90 wt% or less, or 85 wt% or less.
  • composition of one embodiment may be used as a raw material for pharmaceuticals, synthetic resins, synthetic fibers, or dyes.
  • a reactor including a gas-induced type stirrer was prepared.
  • Example 1 the reaction was carried out in the same manner as in Example 1, except that 550 g of CHDA having a trans CHDA ratio of 21 wt% in CHDA was used.
  • Example 1 the reaction was carried out in the same manner as in Example 1, except that 158 g of CHDA having a trans CHDA ratio of 21 wt% in CHDA was used.
  • Example 1 the reaction was carried out in the same manner as in Example 1, except that 34 g of CHDA having a trans CHDA ratio of 21 wt% in CHDA was used.
  • CHDA content means the content (wt%) with respect to the total amount of CHDA and water.

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  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
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Abstract

La présente invention concerne un procédé de préparation de 1,4-cyclohexanediméthanol (CHDM) et, plus particulièrement, un procédé de préparation de 1,4-cyclohexanediméthanol présentant un rapport d'isomères trans élevé même sans inclure d'étape d'isomérisation.
PCT/KR2020/019186 2019-12-27 2020-12-28 Procédé de préparation de 1,4-cyclohexanediméthanol WO2021133137A1 (fr)

Priority Applications (4)

Application Number Priority Date Filing Date Title
JP2022539243A JP2023508201A (ja) 2019-12-27 2020-12-28 １，４－シクロヘキサンジメタノールの製造方法
EP20905622.5A EP4082999A4 (fr) 2019-12-27 2020-12-28 Procédé de préparation de 1,4-cyclohexanediméthanol
US17/789,456 US20230053503A1 (en) 2019-12-27 2020-12-28 Method for preparing 1,4-cyclohexanedimethanol
CN202080093297.4A CN114945546A (zh) 2019-12-27 2020-12-28 制备1,4-环己烷二甲醇的方法

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KR20190176139 2019-12-27
KR10-2019-0176139 2019-12-27
KR1020200183549A KR20210084311A (ko) 2019-12-27 2020-12-24 1,4-사이클로헥산디메탄올의 제조 방법
KR10-2020-0183549 2020-12-24

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US6495730B1 (en) * 1999-09-21 2002-12-17 Asahi Kasei Kabushiki Kaisha Catalysts for hydrogenation of carboxylic acid
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